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Related Concept Videos

Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

6.4K
Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...
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Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

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In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
12.4K
C–C Bond Cleavage: Retro-Aldol Reaction00:57

C–C Bond Cleavage: Retro-Aldol Reaction

7.1K
The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.
7.1K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.8K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.8K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.3K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.3K
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

4.1K
A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Updated: Dec 6, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Electrochemical Oxidation Induced Selective C-C Bond Cleavage.

Shi-Hui Shi1,2, Yujie Liang1, Ning Jiao1,3

  • 1State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.

Chemical Reviews
|October 5, 2020
PubMed
Summary

Electrochemical C-C bond cleavage offers a sustainable alternative to traditional methods. This review highlights recent advances in electrochemically oxidative C-C bond cleavage for organic synthesis and material degradation.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Sustainable Chemistry

Background:

  • Selective carbon-carbon (C-C) bond cleavage is crucial for organic synthesis and macromolecular degradation.
  • Conventional methods often rely on expensive noble metal catalysts and harsh oxidants, impacting sustainability.
  • Electrochemical C-C bond cleavage presents an eco-friendly and scalable alternative using electricity.

Purpose of the Study:

  • To review recent developments in electrochemically oxidative selective C-C bond cleavage.
  • To emphasize synthetic applications and mechanistic insights.
  • To showcase the advantages and potential of electrochemical synthesis.

Main Methods:

  • Review of recent literature on electrochemical C-C bond cleavage.
  • Focus on oxidative cleavage strategies.
  • Analysis of synthetic outcomes and reaction mechanisms.

Main Results:

  • Significant progress has been made beyond traditional Kolbe electrolysis.
  • New electrochemical methods enable selective C-C bond cleavage under mild conditions.
  • Electrochemical synthesis offers a sustainable and efficient approach.

Conclusions:

  • Electrochemical C-C bond cleavage is a promising green chemistry strategy.
  • This approach provides sustainable pathways for organic synthesis and degradation.
  • Further exploration of electrochemical methods holds exciting potential for future chemistry.